Diversity-Oriented Synthesis of Angular Bis-benzimidazole Derivatives under Microwave Irradiation

被引：15

作者：

Chen, Chih-Hau ^{[1
]}

Chien, Ming-Hsien ^{[2
]}

Kuo, Min-Liang ^{[2
]}

Chou, Cheng-Ting ^{[1
]}

Lai, Jin-Ji ^{[1
]}

Lin, Shu-Fen ^{[1
]}

Thummanagoti, Suman ^{[1
]}

Sun, Chung-Ming ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan

[2] Natl Taiwan Univ, Inst Toxicol, Taipei 100, Taiwan

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2009年 / 11卷 / 06期

关键词：

PHASE ORGANIC-SYNTHESIS; CYTOTOXIC METABOLITE; PARALLEL SYNTHESIS; FLUOROUS SYNTHESIS; COMBINATORIAL CHEMISTRY; SUPPORTED SYNTHESIS; LIBRARY-GENERATION; ASSISTED SYNTHESIS; CHEMICAL GENETICS; TRACELESS LINKER;

D O I：

10.1021/cc900084s

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Pharmaceutically interesting, angular bis-benzimidazoles with three appendages have been synthesized successfully through a diversity-oriented approach with soluble support under microwave irradiation. Polymer immobilized o-phenylenediamine was selectively N-acylated with 2-chloro-3-nitrobenzoic acid in a primary aromatic amino moiety. The obtained amide was cyclized to benzimidazole in an acidic condition, and subsequently nucleophilic aromatic substitution with different amines was performed. Successive reduction, cyclization with various aldehydes and activated isothiocyanates yielded angular biheterocyclic benzimidazoles in good quantities. Reaction progress on polymer support was precisely monitored using the conventional proton NMR spectroscopy. Preliminary screening results showed some of these interesting compounds exhibited moderately to good inhibition against vascular endothelial growth factor receptor 3 (VEGFR-3), which is related to invasion and migration of cancer cells.

引用

页码：1038 / 1046

页数：9

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